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. Author manuscript; available in PMC: 2012 Jun 17.
Published in final edited form as: J Org Chem. 2011 May 24;76(12):5092–5103. doi: 10.1021/jo200780x

Table 1.

Deallylative Primary Amidine Formation.

entry amines [5.0 equiv]a amidine products yield [%]b
1 graphic file with name nihms296704t1.jpg graphic file with name nihms296704t2.jpg 11
12
87
2 92
3 graphic file with name nihms296704t3.jpg graphic file with name nihms296704t4.jpg 13
14
15
50
4 71
5 22
6 graphic file with name nihms296704t5.jpg graphic file with name nihms296704t6.jpg 16 30
7 graphic file with name nihms296704t7.jpg graphic file with name nihms296704t8.jpg 17
18
≥95
8 ≥95
a

All entries utilized ynamide 8a except in entry 8, Ph-substituted ynamide 8b was used. All reactions employed 5.0 mol % PdCl2(PPh3)2, 1.0 equiv K2CO3, THF [conc = 0.05 M], 80 °C, 5–8 h.

b

Isolated yields.